Meet The People Who Are Going
To Make Your Florida Roofing Project
A Smooth & Pleasant Experience.

John Woolston – Owner

John is the owner of Montgomery Winslow Roofing Experts. He started in the roofing business when he was just 16. John worked for his father’s roofing company in New York until 1990, when he decided to move to Florida and start his own roofing business. John has over 30 years of roofing experience and has installed thousands of roofs over his career. Though he spends some of his time in the office, John is usually found at ongoing jobsites, personally overseeing the projects, insuring everything is going smoothly. Very few roofers—not just in Florida, but anywhere in the country—can match his knowledge of the industry.

Melissa – Office Manager

Melissa is Montgomery Winslow’s office manager. Her duties include keeping John out of the office, billing, work orders, answering phones, and scheduling estimates and inspections. Melissa has over 30 years of customer-service experience, many of which are in the construction and roofing related business, and is always happy to answer any questions or concerns you may have.

Orlando – Senior Superintendent

Orlando oversees the crews to ensure the job is going smoothly, and also performs all leak and repair estimates. He’s considered the problem-solver because he can assess any situation and come up with the right solution. Orlando has been with Montgomery Winslow since 2001, so he knows the ins-and-outs of the roofing business. Orlando is extremely approachable and will answer any questions you have about your roofing project.

Brad – Executive Supervisor

Brad is John’s son, and has been working at Montgomery Winslow since he was 16. He started in an office position, but began working in the field when he turned 18. Brad’s background in roofing has made him one of the most knowledgeable and skilled installers in Florida. He has his father’s knack for roofing, and it shows in the impeccable work he does.

Dane Smith – Estimator

Dane is Montgomery Winslow’s residential estimator. He is the one who will visit your residence to measure your roof, take before photographs, as well as deliver and explain our company brochure. Dane’s background is in the IT industry and engineering, and he currently serves on the Advisory Counsel for a local university’s IT Department. He is also Melissa’s husband.